Permeable nonaggregating porphyrin thin films that display enhanced photophysical properties

Langmuir

Volumn 20, Issue 24, 2004, Pages 10560-10566

  Splan, Kathryn E ^a   Hupp, Joseph T ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENYL PHOSPHONATES; PHOTOELECTROCHEMICAL PROPERTIES; PHOTOPHYSICAL PROPERTIES; PORPHYRIN THIN FILMS;

ABSORPTION; AMINES; CHROMOPHORES; COLUMN CHROMATOGRAPHY; PHOSPHATES; PHYSICAL PROPERTIES; QUENCHING; REDOX REACTIONS; ZIRCONIUM;

THIN FILMS;

PORPHYRIN;

ARTICLE; ARTIFICIAL MEMBRANE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; METHODOLOGY; PERMEABILITY; PHOTOCHEMISTRY; POROSITY; SPECTROFLUOROMETRY; SPECTROPHOTOMETRY; SYNTHESIS;

ELECTROCHEMISTRY; MEMBRANES, ARTIFICIAL; MOLECULAR STRUCTURE; PERMEABILITY; PHOTOCHEMISTRY; POROSITY; PORPHYRINS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY;

ADSORPTION; AMINES; COLUMN CHROMATOGRAPHY; PHOSPHATES; QUENCHING; THIN FILMS; ZIRCONIUM;

EID: 10044241753     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/1a048465g     Document Type: Article

References (53)

1. Kadish, K.; Smith, K. M.; Guilard, R. The Porphyrin Handbook; Academic Press: New York, 1999.
2. Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461.
3. Abdelrazzaq, F. B.; Kwong, R. C.; Thompson, M. E. J. Am. Chem. Soc. 2002, 124, 4796-4803.
4. Yamada, H.; Imahori, H.; Nishimura, Y.; Yamazaki, L; Ahn, T. K.; Kim, S. K.; Kim, D.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 9129-9139.
5. Tachibana, Y.; Haque, S. A.; Mercer, I. P.; Durrant, J. R.; King, D. R. J. Phys. Chem. B 2000, 104, 1198-1205.
6. Cherian, S.; Wamser, C. C. J. Phys. Chem. B 2000, 104, 3624-3629.
7. Odobel, F.; Blart, E.; Lagree, M.; Villieras, M.; Boujtita, H.; Murr, N. E.; Caramori, S.; Bignozzi, C. A. J. Mater. Chem. 2003, 13, 502-510.
8. Lee, W. W.; Wong, K.; Li, X.; Leung, Y.; Chan, C.; Chan, K. S. J. Mater. Chem. 1993, 3, 1031-1035.
9. Rakow, N. A.; Suslick, K. S. Nature 2000, 406, 710-713.
10. Smith, V. C.; Batty, S. V.; Richardson, T.; Foster, K. A.; Johnstone, R. A. W.; Sobral, A. J. F. N.; Gonsalves, A. M. d. A. R. Thin Solid Films 1996, 284-285, 911-914.
11. Belanger, S.;Hupp, J. T.Angew. Chem., Int. Ed. 1999, 38, 2222-2224.
12. Keefe, M. H.; O'Donnell, J. L.;Bailey, R. C.;Nguyen,S. T.;Hupp, J. T. Adv. Mater. 2003, 15, 1936-1939.
13. Gonsalves, A. M. D. R.; Pereira, M. M. J. Mol. Catal. A 1996, 113, 209-221 and references therein.
14. Merlau, M. L.; Mejia, M. d. P.; Nguyen, S. T.; Hupp, J. T. Angew. Chem., Int. Ed. 2001, 40, 4239-4242.
15. Xu, G.; Yao, N.; Aksay, I. A.; Groves, J. T. J. Am. Chem. Soc. 1998, 120, 11977-11985.
16. Burrell, A. K.; Officer, D. L.; Plieger, P. G.; Reid, D. C. W. Chem. Rev. 2001, 101, 2751-2796.
17. Drain, C. M.; Hupp, J. T.; Suslick, K. S.; Wasielewski, M. R.; Chen, X. J. Porphyrins Phthalocyanines 2002, 6, 243-258.
18. Ungashe, S. B.; Wilson, W. L.; Katz, H. E.; Scheller, G. R.; Putvinski, T. M. J. Am. Chem. Soc. 1992, 114, 8717-8719.
19. Araki, K.; Wagner, M. J.; Wrighton, M. S. Langmuir 1996, 12, 5393-5398.
20. Ruaudel-Teixier, A.; Barraud, A.; Belbeoch, B.; Roulliay, M. Thin Solid Films 1983, 99, 33-40.
21. Ogi, T.; Ohkita, H.; Ito, S.; Yamamoto, M. Thin Solid Films 2002, 415, 228-235.
22. Ni, Y.; Puthenkovilakom, R. R.; Huo, Q. Langmuir 2004, 20, 2765-2771.
23. Udal'tsov, A. V.;Kazarin, L. A.; Sweshnikov, A. A. J. Mol. Struct. 2001, 562, 227-239.
24. Bedioui, F.; Devynck, J.; Bied-Charreton, C. Acc. Chem. Res. 1995, 28, 30-36.
25. Hofkens, J.; Latterini, L.; Vanoppen, P.; Faes, H.; Jeuris, K.; Feyter, S. D.; Kerimo, J.; Barbara, P. F.; Schryver, F. C. D.; Rowan, A. E.; Nolte, R. J. M. J. Phys. Chem. B 1997, 101, 10588-10598.
26. Loss of emission upon film formation has been documented for many years, beginning with Irving Langmuir himself, as observed in thin films of chlorophyll layers. Langmuir, I.; Schaefer, V. J. J. Am. Chem. Soc. 1937, 59, 2075-2076. We thank a reviewer for drawing our attention to this paper.
27. Imahori, H.; Norieda, H.; Nishimura, Y.; Yamazaki, I.; Higuchi, K.; Kato, N.; Motohiro, T.; Yamada, H.; Tamaki, K.; Arimure, M.; Sakata, Y. J. Phys. Chem. B 2000, 104, 1253-1260.
28. Nolte, R. J.; Razenberg, J. A. S. J.; Schuurman, R. J. Am. Chem. Soc. 1986, 108, 2751-2752.
29. Massari, A. M.; Gurney, R. W.; Huang, C. H. K.; Wightman, M. D.; Nguyen, S. T.; Hupp, J. T. Polyhedron 2003, 22, 3065-3072.
30. Katz, H. E. Chem. Mater. 1994, 6, 2227-2232.
31. Nixon, C. M.; LeClaire, K.; Odobel, F.; Bujoli, B.; Talham, D. R. Chem. Mater. 1999, 11, 965-976.
32. Muthukumaran, K.; Loewe, R. S.; Ambroise, A.; Tamaru, S.; Li, Q.; Mathur, G.; Bocian, D. F.; Misra, V.; Lindsey, J. S. J. Org. Chem. 2004, 69, 1444-1452.
33. Loewe, R. S.; Ambroise, A.; Muthukumaran, K.; Padmaja, K.; Lysenko, A. B.; Mathur, G.; Li, Q.; Bocian, D. F.; Misra, V.; Lindsey, J. S. J. Org. Chem. 2004, 69, 1453-1460.
34. Cao, G.; Hong, H. G.; Mallouk, T. E. Acc. Chem. Res. 1992, 25, 420-427.
35. Snover, J. L.; Byrd, H.; Suponeva, E. P.; Vicenzi, E.; Thompson, M. E. Chem. Mater. 1996, 8, 1490-1499.
36. Vermeulen, L. Prog. Inorg. Chem. 1997, 44, 143-146.
37. Mallouk, T. E. Acc. Chem. Res. 1998, 31, 209-217.
38. Clearfield, A. Chem. Mater. 1998, 10, 2801-2810.
39. Massari, A. M.; Gurney, R. W.; Schwartz, C. P.; Nguyen, S. T.; Hupp, J. T. Langmuir 2004, 20, 4422-4429.
40. Splan, K. E.; Massari, A. M.; Hupp, J. T. J. Phys. Chem. B 2004, 108, 4111-4115.
41. Gurney, R. W.; Nguyen, S. T.; Hupp, J. T. Manuscript in preparation, 2004.
42. Deniaud, D.; Schollorn, B.; Mansuy, D.; Rouxel, J.; Battioni, P.; Bujoli, B. Chem. Mater. 1995, 7, 995-1000.
43. Senge, M. O.; Medforth, C. J.;Forsyth, T. P.; Lee, D. A.; Olmstead, M. M.; Jentzen, W.; Pandey, R. K.; Shelnutt, J. A.; Smith, K. M. Inorg. Chem. 1997, 36, 1149-1163.
44. Uyeda, H. T.; Zhao, Y.; Wostyn, K.; Asselberghs, I.; Clays, K; Persoons, A.; Therien, M. J. J. Am. Chem. Soc. 2002, 124, 13806-13813.
45. Laha, J. K.; Dhanalekshmi, S.; Taniguchi, M.; Ambroise, A.; Lindsey, J. S. Org. Process Res. Dev. 2003, 7, 799-812.
46. Arsenault, G. P.; Bullock, E.; MacDonald, S. F. J. Am. Chem. Soc. 1960, 82, 4384-4390.
47. Littler, B. J.; Ciringh, Y.; Lindsey, J. S. J. Org. Chem. 1999, 64, 2864-2872.
48. McKenna, C. E.; Higa, M. T.; Cheung, N. H.; McKenna, M. C. Tetrahedron Lett. 1977, 2, 155-158.
49. Anderson, H. L. Tetrahedron Lett. 1992, 33, 1101-1104.
50. DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993.
51. Kasha, M.; Rawls, H. R.; El-Bayoumi, M. A. Pure Appl. Chem. 1965, 11, 371-392.
52. Anderson, H. L. Inorg. Chem. 1994, 33, 972-981.
53. Note that, in contrast to 2, Milic and co-workers have demonstrated that porphyrin tetramers with alkane appendages can form nearly uniform films wherein there is little evidence of intersquare interactions, as evidenced by atomic force microscopy (ATM). Photophysical behavior has yet to be reported. Milic, T.; Garno, J. C.; Batteas, J. D.; Smeureanu, G.; Drain, C. M. Langmuir 2004, 20, 3974-3983.